


but if you try sometimes you just might find

by madapricot



Category: Supernatural
Genre: Alternate Universe - Prostitution, Anal Sex, BDSM, Bad BDSM Etiquette, D/s, Feminization, M/M, Restraints, Rough Oral Sex, Satin Panties, Top!Cas, john!cas, prostitute!Dean
Language: English
Status: Completed
Published: 2014-01-02
Updated: 2014-01-02
Packaged: 2018-01-07 03:10:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,766
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1114781
Author URL: https://archiveofourown.org/users/madapricot/pseuds/madapricot
Summary: <blockquote class="userstuff">
              <p>Dean turns a trick for a blue-eyed john who puts him in silk panties and ties him up before giving him the best orgasm of his life. Mysterious ways, indeed.</p>
            </blockquote>





	but if you try sometimes you just might find

**Author's Note:**

> I wrote this for someone on my old tumblr, hence the slapdash capitalization and quotations. I hope it isn't too distracting.

'gentle with the merchandise,' dean growls, but he's savoring the faint taste of blood and the way his cheek throbs. a good hit like that is a shock to the system, makes the dingy room hyperreal for a split second, makes his head feel like it's having its own little orgasm, filling up with fireworks and heat. he's lingering on that sensation as the john pushes him forward, face in the sheets, arms firmly bound and cock rutting helplessly into silk ruffles.

  
he turns his face as best as he can, still half-buried in the bed. 'you like it when they can't run away, huh?' the john just glares, slides his broad hands over dean's satin-wrapped ass and roughly pulls his cheeks apart, presses his thumbs in a firm drag against dean's hole. the sheer possessiveness is enough to make dean's cock twitch, hard, but he doesn't start to lose it until the john leans over dean's naked back, thumbs still grinding hungrily into his opened ass, breathing hot against his neck. he's naked, yeah, but now he feels vulnerable. owned.

‘i like when they want it,’ the john rumbles, low and rough against dean’s ear, “but pretend they don’t,’ and dean can’t stop himself from actually fucking shivering when the dude licks the side of his neck. the hands release his ass and dean’s scrambling together the brain cells for a smart response to the smug look on the john’s face as he sits up and removes his blue tie. he doesn’t have a chance, though, before the tie is shoved between his teeth, tasting of salt and silk.

  
‘it’s a placeholder,’ the john says as his suit jacket joins his trenchcoat on the motel chair and dean splutters around the tie in his mouth. ‘you’re very pretty, but you talk too much.’ back at the edge of the bed, he grabs a handful of hair, none too gentle, pulls dean’s head back as he thrusts against dean’s panty-clad ass, and even through at least three layers of clothes his cock is hot and rock-hard. dean moans, and there’s a smile in the john’s voice. ‘better.’

  
‘later, i'm going to keep you quiet with my cock,’ the john says, matter of fact, like you'd comment on the likelihood of rain this afternoon, still holding him by the hair, but his unseen other hand isn't idle. there’s the surprise of cold lube dribbling onto the small of dean's back, leaking down his ass crack, making the silk panties cling, damp, to his skin. dean jerks against the sensation, and he’s dropped back onto the bed. this dude is turning out to be a much bigger freak than dean anticipated—serves him right for trusting the accountant garb—and he’s beginning to wonder if he’ll escape this in one piece.

  
maybe the worry is evident on his face. the john pats his still-throbbing cheek, then pushes aside the satin panties to work two fingers against dean's wet hole, blue eyes intent on dean's. 'you'll like this, you little slut' he promises, as his fingers stroke and press and push, the pleasant intrusion beginning to rebuild the buzz in his cock. they all want him to like it; they all want to leave confident in their prowess, but this son of a bitch might actually do it for him, the way he's rough but thorough, self-interested but still carefully readying dean to be fucked. dean's trying to keep his head together, trying not to get too lost in it, when the john spanks him, a stiff-handed crack across the bottom of his ass and the back of his thigh. the unexpected sharpness makes dean yelp into the tie in his mouth, involuntarily pull away from the fingers confidently prepping his ass.  
  
"hold still," the john growls, and the fingers are no longer teasing and readying but push forcefully into his ass, slick and hot. dean forces himself to freeze, fights the still-fresh instinct to pull away, that something is wrong, when the john spanks him again.

  
"stop tensing," he says, working his fingers in and out of dean's hole between flurries of blows, sharp and attention-getting, enough to let dean taste that place where pain is just sensation and his whole soul can ride it like a kite, but not harmful. it's a point of pride for dean to conquer his gut reactions, to relax into the hands on and in his ass--  
"take it like a good whore, yes," says the john, his voice almost soothing. dean makes his eyes refocus, to register the hungry look on the man's face as he adds a third finger to dean's ass. when he catches dean watching his expression smooths back into cold amusement. 'you're tight for a cockslut.'

  
dean scowls around the tie--it's soaked with drool and must look ridiculous, hanging out of his mouth like that--and shoves back against the fingers, petulant. show you a cockslut, he thinks, and the john grins, slaps his thigh again, harder. 'knew you wanted it,' and he pulls his fingers out of dean, stands up straight and unbuckles his belt, eyes on dean's the whole time. 'in fact, i think you might need it.'

  
for all his braggadacio the john doesn't waste any time stripping himself the rest of the way. he moves out of dean's limited view for a moment and dean recognizes the rustling of a condom wrapper. but instead of taking dean as he is--and his ass is begging to be taken as it is, hanging empty in the air--he rolls dean over, tied arms trapped underneath his body, precariously close to the edge of the bed, legs pressed nearly to his chest. it's uncomfortable, but dean doesn't notice, too busy eyeing the john's hard cock, his runner's body, his skin which looks like it will be hot to the touch, molded above him. he looks more natural, more relaxed naked--and more predatory, as he palms dean's cock through the panties, leers at the way his body is contorted and leans in, pressing dean's legs even further open and down as pushes the panties aside more firmly, lines his cock up with dean's ass.

  
he slides in, slowly, letting dean adjust, carefully studying dean's face, and it's a struggle against letting his eyes roll back in his head with the sensation of it. 'good boy,' the john purrs, and dean gasps around the tie, those words hitting him like a solid punch to the gut. his response isn't missed; the john wraps his hand around dean's satin-swathed cock, presses his thumb firmly to the underside of its head and holding there as he begins to slowly, shallowly fuck dean's ass.

  
'good boy,' he repeats, giving dean's cock a squeeze, and the fullness in his ass and the cool smoothness of the satin and that grip, which teases the head of his cock but doesn't jerk him off and those words, those fucking words are like a hook in his belly and for someone who complained that dean talked too much the john won't shut up, too into the sound of his own voice but dean is pretty well into it too if his desperate attempts at thrusting himself harder on the john's cock, thrusting himself against the john's hand are any indication.

  
'i don't want you to hold out, you pretty little thing. i want you to come hard and fast for me. be my good boy.'

  
he can't look anymore, he can't stand those blue eyes taking him apart, not when he's this close, so he throws his head back, grateful for the way the tie muffles his moans. the john's picking up speed, fucking into him harder and deeper, leaning on one hand while his other keeps dean's cock trapped and teased, times his thrusts and his squeezes, fast and final, leaning in to growl in that sandpaper voice. 'come for me. come for me, now.' and it's over, his body mimics the universe and simultaneously expands and contracts and explodes all at once, his whole being united in one long animal scream of light and sound and sensation.

  
he's not aware of the john pulling out, not aware of anything until the tie is taken from his mouth and he's being dragged to the floor, to his knees, blinking and gasping stupidly from the aftershock. his cock is softening in come-wet panties and the john is watching him struggle to stay upright with that same fucking smug expression on his face.

  
'you were a very good boy,' he says and his cock, stripped of its condom, is pressed against dean's lips. 'continue to impress me,' he demands, and dean yields easily, opens his mouth and lets the john guide his head with a fistful of hair. he's not gentle--he fucks dean's mouth, gags and chokes him with that long cock--but he's brief, just a few deep thrusts and then he's holding dean in place, a cocksheath while he grinds and gasps and mutters, all garbled 'fuck's and 'good's and come bubbles out of the corner of dean's mouth.

  
when he pulls out of dean's mouth he's panting, wild-eyed, stares at the come dripping from dean's chin for a long moment. then, wordless, his face quickly closing, he steps behind dean and unties the rope binding his arms.

  
dean stumbles to his feet, unsteady, grabs his jeans from the floor. the usual post-trick awkwardness is about ten times worse than usual, the shame over how hard he came, how much he enjoyed being called a good boy replacing the languidness in his limbs with salt and iron.

  
the john is sitting on the bed behind him, not bothering to reach for his own clothes. 'aren't you forgetting something?' he asks, the amusement returned to his voice. he got the money up front, safely tucked in his jacket, so of course he hasn't forgotten--oh. he's one leg in his jeans when he realizes he's still wearing the ruffled satin panties, soaked as they are with come and lube.

  
'um. right.' dean coughs to hide his embarrassment, awkwardly strips the damp fabric off, tosses it in the john's direction.

  
later he wishes he could have walked off with them, keep them to stuff in his mouth or wear while jerking off--probably exactly what the john had in mind. the thought is way more arousing than it should be, fueling his fantasies for weeks afterwards, gives him somewhere good to go when less courteous men are fucking his mouth and ass.


End file.
